Many comments below focus on failures with a single startup. I think it misses the point. Working for startups is risky, but the key is to build a system that increases your accumulated probability of success -- this is exactly why it's important to live in the bay area and work for some startups there, at least before the Covid-19. You get to see a large number of people who didn't fund any company, but still became financially independent by choosing to join the right companies at the right time. You get to see how those people make their choices. You get to see how those people decide to jump ship. You get to build a social circle where you learn lots of first-hand information about startups. There are a few simple steps that worked well for many people (again, no guarantee of success, but they do increase accumulated probability of finding the right company).

- You bet on product you love. Airbnb/Pinterest/Uber before 2013, Netflix before 2010, FB before 2009, Google before 2003, Databriks before 2017, Tesla before 2017.

- You bet on sectors. SDN, gig economy, search, big data, and etc.

- You bet on company's productivity - the customers/engineer grows exponentially without Uber-style marketing cost - Instagram/WhatsApp; the company releases features faster than they hire - Google; people deliver without working like a dog - Netflix

- You bet on people you know or you admire

- You bet on the leaders in each sector